Triethylamine → HCID 57444160, compound

HRID 44645Notes

Reaction equation

HRID 44645 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]([Cl:11])=[O:10])[CH2:5][CH2:4]1.Cl.[OH2:13].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=O.C(N(CC)CC)C>ClCCl>[ClH:11].[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]([N:14]2[CH2:19][CH2:18][C:17](=[O:13])[CH2:16][CH2:15]2)=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 22021827Piperidone monohydrate hydrochloride

Product 1

HCID 57444160HCID 57444160, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-methylpiperazine-1-carbonyl chloride hydrochloride (19.9 g 0.1 mol) and piperidone monohydrate hydrochloride (15.3 g 0.1 mol), in 200 mL of dichloromethane, dry triethylamine (45 mL, 0.33 mol) was added dropwise. The mixture was stirred for 2 hours. The organic phase was washed with brine (2×20 mL) and dried over sodium sulfate. After filtration, the solvent was evaporated in vacuo and the crude product was dissolved in EtOH (50 mL) and diethylether (100 mL) and treated with HCl 4N in dioxane (25 mL). After 1 hour, the precipitate was filtered and dried in oven to give 13 g (yield 50%) of the title compound.

Workup

  1. washThe organic phase was washed with brine (2×20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated in vacuo
  5. dissolutionthe crude product was dissolved in EtOH (50 mL)
  6. additiondiethylether (100 mL) and treated with HCl 4N in dioxane (25 mL)
  7. waitAfter 1 hour
  8. filtrationthe precipitate was filtered
  9. customdried in oven

Sources & evidence

ORD record
ord-64ff0a64e8ce4469a9ff38d93ccfe498
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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